N-(Chloromethyl)phthalimide
- CAS NO.:17564-64-6
- Empirical Formula: C9H6ClNO2
- Molecular Weight: 195.6
- MDL number: MFCD00005898
- EINECS: 241-541-4
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-07-30 17:04:37
What is N-(Chloromethyl)phthalimide?
Chemical properties
white crystalline powder
The Uses of N-(Chloromethyl)phthalimide
It is used as an agrochemical and medicine intermediates and is used in organic synthesis. Microporous membranes prepared from chemically modified polysulfone, which is a derivative of this compound have better streaming potential.
What are the applications of Application
N-(Chloromethyl)phthalimide is a chlorine derivative of Phthalimide. Phthalimide and its derivatives are essential compounds in diverse fields. In pharmaceuticals, they are used as an intermediate material. In the medical field, they are used to synthesize compounds with antimicrobial activity, androgens, and other agents for treating tumor necrosis factor. Certain phthalimide derivatives are used as herbicides and to reduce bacterial contamination. They are widely used in industries to produce pesticides, plastics, resins, and surfactants. The N-substitution of the Phthalimide has a hypsochromic effect on color change and better color yields on poly fabrics because of the electron-donating property of the methyl group and the higher hydrophobicity of Phthalimide. Its chlorine derivative is used as an intermediate for producing medicine, pharmacy, dyes, pesticides, fire retardants, and photocopying chemicals. In particular, N-(bromomethyl)phthalimide and N-(chloromethyl)phthalimide play a vital role in anti-inflammatory, analgesic, and hypolipidimic activities[1].
Purification Methods
Purify the imide by recrystallisation from EtOAc or CCl4 or via the 1:1 complex with pyridine [Sakellarios J Am Chem Soc 70 2822 1948, B.hme et al. Chem Ber 92 1258 1959]. [Beilstein 21/10 V 372.]
References
[1] V. Balachandran , S. Rajeswari, S. Lalitha . “Density functional theory, comparative vibrational spectroscopic studies, NBO, HOMO–LUMO analyses and thermodynamic functions of N-(bromomethyl)phthalimide and N-(chloromethyl)phthalimide.” Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 91 (2012): Pages 146-157.
Properties of N-(Chloromethyl)phthalimide
Melting point: | 131-135 °C (lit.) |
Boiling point: | 305.2±25.0 °C(Predicted) |
Density | 1.3228 (rough estimate) |
refractive index | 1.5790 (estimate) |
storage temp. | 2-8°C |
solubility | chloroform: soluble50mg/mL |
form | powder to crystal |
pka | -2.63±0.20(Predicted) |
color | White to Almost white |
Water Solubility | slightly soluble |
BRN | 140942 |
InChI | InChI=1S/C9H6ClNO2/c10-5-11-8(12)6-3-1-2-4-7(6)9(11)13/h1-4H,5H2 |
CAS DataBase Reference | 17564-64-6(CAS DataBase Reference) |
NIST Chemistry Reference | N-(chloromethyl)phthalimide(17564-64-6) |
EPA Substance Registry System | 1H-Isoindole-1,3(2H)-dione, 2-(chloromethyl)- (17564-64-6) |
Safety information for N-(Chloromethyl)phthalimide
Signal word | Danger |
Pictogram(s) |
Skull and Crossbones Acute Toxicity GHS06 |
GHS Hazard Statements |
H301:Acute toxicity,oral H315:Skin corrosion/irritation H317:Sensitisation, Skin H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for N-(Chloromethyl)phthalimide
InChIKey | JKGLRGGCGUQNEX-UHFFFAOYSA-N |
SMILES | C1(=O)C2=C(C=CC=C2)C(=O)N1CCl |
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